At this point, most of us have planned our summer travel, but there’s no reason our journeys have to end when the air starts to chill.
We’ve rounded up the best upcoming chic destinations for you, depending on your part of the country—because travel expenses aren’t just about where you’re going, they’re also about where you’re coming from. A quick and inexpensive trip for some might require hours in the air and thousands of dollars for others (Hawaii and London come to mind as quick jaunts for the West and East Coast respectively; not so much for the reverse coasts).
We’ve divided our favorite chic and inexpensive getaways by region, so you can spend less time and money in the air, and more where you want to—on the ground.
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If You’re Traveling From the Northeast
Iceland A hot new destination, it’s close to the Northeastern United States and affordable compared to the rest of Western Europe. Iceland Air has a great stopover option which allows travelers to explore Iceland en route to (or on their way back from) more than 20 destinations served by the airline, for the cost of a single flight. For example: Depart Boston on September 9, hang out in Reykjavik for a few days, and then head on to London on the 12th, all for $439 including taxes and fees. Despite the economic crisis that nearly turned Iceland into a barter economy just a few years ago, hotel prices still haven’t dropped to what we’d call “cheap” levels. But deals are certainly available. At the Hótel Frón, rooms in September start at $139 per night.
Portugal Portugal is a great destination for lovers of food, culture, and history. With a ton of castles, museums, music venues, delicious eateries, and kind, English-speaking locals (all just a few hours from the U.S.), it’s the perfect long weekend. One way to score an inexpensive flight is to fly from the East Coast to a major hub like London or Madrid, which tends to be less expensive than flying to Portugal directly. From there, try out a low-cost European airline like EasyJet for the short intra-European leg. In October, you can get from London to Lisbon for as little as 14 British pounds each way. (To play with the numbers, try out Skyscanner.)
In Lisbon, the Hotel Vip Executive Diplomático is located in a quiet neighborhood near the incredible Castelo Sao Jorge and Parque Eduardo VII. For about $120 per night in October, you get a sizable room with a plentiful breakfast. For just $10 more, upgrade to luxury at the Tiara Park Atlantic Hotel, just a few blocks away. A short drive north from Lisbon along the coast leads to Porto, a beautiful city in the Douro River Valley that is a UNESCO World Heritage Site. Here, prices dip even lower than in the capital. October rates at the centrally-located, four-star Mercure Porto Centro start at just $72.
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If You’re Traveling From the Southeast
Bermuda From its friendly locals to its beautiful beaches, fascinating colonial history, glorious seafood, and wide range of lodging options, the tiny archipelago has a ton to offer (beyond those fabulous shorts).
The downside of Bermuda is its high GDP, which means that visiting the island can be a pricey undertaking—but not if you know where to go. Instead of staying at one of the big name resorts (Fairmont or Mandarin Oriental) where the cheapest rooms can run you upwards of $400 per night, check into a smaller guesthouse or B&B. These are tiny enclaves of British colonial hospitality where the proprietors treat guests like long-lost cousins. The cozy Greenbank Guesthouse & Cottages is a short ferry ride from the city of Hamilton. A garden view room with a kitchenette is $175 per night. An apartment with room for four is just $320 per night (that’s $80 per person).
Another option is the Oxford House, just across the water in Hamilton. This stately townhouse feels like a step back in time when people dressed up in morning coats and prim hats for luncheon. A double here is $246 per night, but like Greenbank, it pays to bring friends—a quad room is $346, or $86 per person. Both properties include breakfast in the room rate.
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If You’re Traveling From the West Coast
Baja Peninsula (But Not Where You’re Thinking) That long strip of land stretching from southern California down alongside the Sea of Cortez has come to be defined by the spring break party town that is Cabo San Lucas. But if you’re looking for something more authentic (and less “daiquiri in a foot-long plastic glass”), stay in the quiet artsy town of Todos Santos, 75 miles north of Cabo. The later fall months are shoulder season (the time between high and low tourist season), which means cheaper flights (around $400 roundtrip from Los Angeles and $600 from Seattle) and fewer tourist throngs.
Rancho Pescadero is the hidden gem of Baja. This incredible 27-room hotel combines luxurious amenities and top-notch service with a casual, shoes-optional vibe, and is located right on the Pacific Ocean where sightings of surfers and whales are the norm. There are no TVs or phones (though free WiFi is available for addicts), and activities include yoga, kayaking, stargazing, laying around, and eating homegrown organic food. Rooms are large, with balconies, and start at $185.
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If You’re Traveling From the Midwest
Toronto, Canada Foodies and architecture buffs flock to Toronto for its diverse selection of cuisine (from Azerbaijani to Laotian) and eye-popping buildings (Frank Gehry’s Art Gallery of Ontario, Will Alsop’s Sharp Centre for Design, and Daniel Libeskind’s Michael Lee-Chin Crystal wing of the Royal Ontario Museum).
Canada’s new low-cost carrier Porter Airlines has direct daily flights from Chicago for around $400, including complimentary snacks, wine, and beer (you read that right—free booze on a flight!). The Novotel Toronto Centre is a grand property and a great value in downtown, with rates starting at around $150 per night. For something a bit trendier, check into the Drake Hotel in the artist-filled Queen West neighborhood. This 19-room property has performance art installations in the lobby and a crush of partiers waiting to get into its unspeakably cool bar on the weekends. Rooms here start at about $200 per night.
Even if you are one of the hip kids staying at the Drake, you must try a poutine in Toronto. Although it sounds harmless (charming, even), don’t be fooled. Poutine is a street snack made of french fries, gravy, and cheese curd. Heart valves beware!